Asymmetric Reduction of Aromatic Ketones. II. An Enantioselective Synthesis of Methyl(2R,3S)-3-(4-Methoxypehnyl)glycidate.

Matsuki, Kenji; Sobukawa, Masao; Kawai, Akiyoshi; Inoue, Hirozumi; Takeda, Mikio

doi:10.1248/cpb.41.643

Cited by 36 publications

(18 citation statements)

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“…The NMR chemical shifts were in good agreement with those published in the literature for compounds 1 [ 21 ] , 2 [ 22 ] , and 4 [ 23 ], while according to our literature search, compound 3 has not yet been reported. However, stereoisomers of the structurally highly similar 4-OMe derivative have been the subject of many investigations [ 24 , 25 , 26 ]. Our NMR data are in good agreement with those reported by Matsuki et al [ 24 ].…”

Section: Resultsmentioning

confidence: 99%

AAPH or Peroxynitrite-Induced Biorelevant Oxidation of Methyl Caffeate Yields a Potent Antitumor Metabolite

et al. 2020

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Hydroxycinnamic acids represent a versatile group of dietary plant antioxidants. Oxidation of methyl-p-coumarate (pcm) and methyl caffeate (cm) was previously found to yield potent antitumor metabolites. Here, we report the formation of potentially bioactive products of pcm and cm oxidized with peroxynitrite (ONOO¯), a biologically relevant reactive nitrogen species (RNS), or with α,α′-azodiisobutyramidine dihydrochloride (AAPH) as a chemical model for reactive oxygen species (ROS). A continuous flow system was developed to achieve reproducible in situ ONOO¯ formation. Reaction mixtures were tested for their cytotoxic effect on HeLa, SiHa, MCF-7 and MDA-MB-231 cells. The reaction of pcm with ONOO¯ produced two fragments, an o-nitrophenol derivative, and a new chlorinated compound. Bioactivity-guided isolation from the reaction mixture of cm with AAPH produced two dimerization products, including a dihydrobenzofuran lignan that exerted strong antitumor activity in vitro, and has potent in vivo antimetastatic activity which was previously reported. This compound was also detected from the reaction between cm and ONOO¯. Our results demonstrate the ROS/RNS dependent formation of chemically stable metabolites, including a potent antitumor agent (5), from hydroxycinnamic acids. This suggests that diversity-oriented synthesis using ROS/RNS to obtain oxidized antioxidant metabolite mixtures may serve as a valid natural product-based drug discovery strategy.

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Section: Resultsmentioning

confidence: 99%

AAPH or Peroxynitrite-Induced Biorelevant Oxidation of Methyl Caffeate Yields a Potent Antitumor Metabolite

et al. 2020

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“…25,26 [RuCl 2 (p-cymene)] 2 was prepared following the reported procedure. 27 NMR spectra were recorded in CDCl 3 on a Varian Inova-400 or Varian System-300 NMR spectrometer at 400 or 300 MHz for 1 H and 100 or 75 MHz for 13 C NMR with TMS as an internal reference. Enantiomeric excess (ee) and diastereomeric ratio (dr) determination were carried out using HPLC analysis with a Daicel Chiralcel OD-H, IA or OJ-H column using hexane/isopropanol as the …”

Section: Methodsmentioning

confidence: 99%

“…In addition, they can be converted into α-amino-β-hydroxy acids with a direct nucleophilic substitution of the chlorine atom. [10][11][12] Now many methods have been developed for the enantioslective synthesis of them, including hydride reduction, 13 catalytic hydrogenation 14,3 or biocatalytic reductions 1,15,16 of the corresponding 2-chloro-3-oxo esters, nitrous halogeno-deamination of natural α-amino-β-hydroxy acids, 17,18 and so on. Asymmetric transfer hydrogenation (ATH) is a mild methodology for the catalytic asymmetric reduction of C＝O or C＝N double bonds.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Reduction of 2‐Chloro‐3‐oxo Esters by Transfer Hydrogenation

Bai

Miao

et al. 2011

Chin. J. Chem.

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“…1 and 2, is a typical calcium channel blocker and is used clinically as an effective antianginal and antihypertensive agent in more than 100 countries (1). Many methods have been investigated for the synthesis of this optically active medicine (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). On a commercial basis, the standard process of nine chemical synthetic steps had been used for a long time.…”

Section: Diltiazemmentioning

confidence: 99%